Charlottesville Travel Guides (Updated September 2026)

Sterling gave an amazing tour! He packed so much knowledge and history into my extended tour for me!

Five friends deciding to do a wine tour and trying to decide if this was worth the money. The answer is YES, worth every penny. Our five hour tour gave us a remote pick up, three wineries (with lunch at one) the knowledge from our driver about the wineries we were visiting and the ability to enjoy our visits while traveling safely. A special thanks to our driver Joe…..

Loved Danielle! She was so fun and sweet. Two very different winery’s, both nice. Short walk to ruins and beautiful at Barboursville Vineyards, and we were able to bring our wine for the walk. Love the prix fixe curations at early mountain. Bison was soooooo good!

We absolutely loved this guide so much so that we will buy another guide for another destination.One issue we faced was not being able to increase the volume. Even though the phone volume was at max and we tried adjusting the car volume, it was just not getting any louder. It was fine for the most part, but if my kids were a bit older, they might have complained that they couldn't hear the guide in the backseat of the car.The guide itself was very helpful and entertaining and made our trip much more enjoyable.

Gillie was the best and made our day so special!

Our wine tour was absolutely amazing! Gillie was the best driver. He was so kind and courteous. I would definitely book with them again!

Thank you sooo much to Melissa!! She was on time, friendly and professional! She also gave us recommendations on wineries which was so helpful!! We would definitely book again!

The entire trip was amazing! Jeff was an excellent guide and took the time with us to explain so much about the area! Event was well organized and safety was a priority. Food was fresh and the two winery stops were very pretty and welcoming!!!

Kathleen was so incredibly knowledgeable and adaptable. I was traveling with my 10 year old grandson who is quiet but totally soaked everything in. We were so fortunate to have such flexibility as we were the only two on our trip. Definitely so worthwhile.

Very informative and easy to follow. My husband and I enjoyed the tour a lot and plan on using it again in the future.

Ole Crow Tours makes wine touring convenient and easy to schedule. Let me explain:Our group of 4 were staying at a B&B in Orange - a location not normally on their list for tour pickups but when asked via email if they could manage this, within moments they replied back that they would indeed pick us up at this location with no additional charge. Fast and easy.When the day of our scheduled tour arrived, Keith our driver for the afternoon, was super prompt and out of the van ready to assist us get comfortable on our way to the 1st of 3 destinations.Reservations had already been made by Ole Crow Tours at all 3 of our winery destinations so no wait, no fuss - just prompt seating and enjoyable tastings pared with food at all 3 stops. (Food and wine are not included in the cost of the private tour so be sure to bring payment for those items that you'll consume.)Ole Crow Tours scheduled us to visit 3 wineries during our 5 hour tour which covered a range of venues and styles. Each stop offered its own vibe and unique character and each showcased the splendid wines and hospitality of Virginia's premier wine country.We appreciate the professionalism of Ole Crow Tours throughout the planning and execution phases of our trip. We would recommend them to anyone interested in winery tours without the risk of drinking and driving. This is the way to go.

Very professional, take you anywhere you wanna go also offer great recommendations. Went with three couples everybody had a very good time.

This was a wonderful way to get an overview of the park. I used the app via CarPlay in my car, and the app knew our location via GPS. It was very informative, and well worth the cost. I would certainly do this again in our next National Park visit.I had not received the code via email to start the app, but I was able to resolve the issue with a 5 minute phone call, so all was well. Make sure to download the tour contents before entering the park. We did it before leaving the hotel wifi.Unfortunately, the weather was cloudy/overcast so we could not always observe the features described -- but at least we had the description from the audio tour. We jumped off the tour to explore Luray Caverns, then returned to resume the tour. It is a long tour, since the speed limit is only 35. We ended up cutting the tour short to drive on towards Gettysburg for our next stop on the trip.

The guide was reading off her phone. That's not a tour. Zero personality. Not recommended. Couldn't answer questions.

We had a terrific time, which was 100% enhanced by the audio narrative; interesting and informative. It was cloudy one day so we went back on a sunny and was able to use the narrative both days. Highly recommended

Great experience. Visited some excellent spots. Ride was clean and comfortable. Will go back and do it again one day